Real Reasons Behind 16-Year Oprah-Letterman Feud

Was it really just a prank in which David Letterman saddled Oprah Winfrey with his lunch bill that caused a 16-year rift between the two? No, says celebrity biographer Kitty Kelley. The reasons for the animosity go much, much deeper.

It was Letterman's failure to defend Winfrey from an unruly audience member when she was a guest on his show in the '80s and a series of subsequent digs 'The Late Show' host made at Winfrey's expense that cemented their rivalry, Kelley writes in The Huffington Post.

Letterman told Jon Stewart last week on 'The Daily Show' that his Oprah battle stemmed from an incident at a restaurant where they were both having lunch. The comedian jokingly told the waiter that Oprah had agreed to pick up his tab, waving at her to prove his point. The waiter was convinced, and put Letterman's lunch on Winfrey's bill.

"That pissed her off," Letterman said. "Not everyone likes horse play."

But that was only the tip of the iceberg. Kelley claims the contempt between the two talk show legends actually began in 1989, after Oprah hosted a controversial segment on devil worship that almost sank her career and her credibility. Complaints streamed in from viewers accusing Winfrey of failing to question her guest's claims that her family prayed to Satan and sacrificed babies.

Though Letterman didn't mention the episode when Winfrey appeared on his show the night after, his questions appeared to ruffle her, and his audience didn't seem sympathetic to Oprah. The interview became more awkward after a man in the crowd shouted, "Rip her, Dave!" and he did nothing to defend her, according to Kelley -- who implied that Letterman may have been drunk that night.

"I think she resented the fact that I didn't rise to the occasion and, you know, beat up on the guy," the comedian said several years later. "Which I probably should have, but I was completely out of control and didn't know what I was doing."

It didn't stop there. A few nights after his Winfrey interview, Letterman quipped to his audience that he was sick after eating claims at Oprah's restaurant, The Eccentric. Oprah had had enough. She stopped speaking to Letterman and kept her distance for the next 16 years.

A series of potshots the 'Late Show' host took at her during that time only made Oprah hate him more, Kelley says. When he hosted the Oscars and pretended to confuse Oprah's name with Uma Thurman's, Winfrey was furious.

He set her off again when he did a "Top 10" list of articles that might appear in her newly launched O, The Oprah Magazine, in 2000: No. 10: P, R, A and H, the four runner-up titles for this magazine; No. 6: The night I nailed Deepak Chopra; No. 4: My love affair with Oprah, by Oprah.

Letterman continued to make Winfrey the butt of many of his jokes. By then, she had a cult following and everyone was clamoring to be one of her guests -- including, oddly, Letterman. He began an "Oprah blog" in which he pleaded to be invited on her show, and he repeatedly told his audience, "It ain't Oprah til it's Oprah." His fans joined in, holding up signs saying, "Oprah, Please Call Dave."

She refused, until 2005 when she finally broke her silence. She agreed to be a guest on his show and then allowed him to accompany her to the Broadway musical that she produced, 'The Color Purple.' Letterman was the perfect gentleman, tripping all over himself in deference to Oprah.

The kiss-and-make-up session didn't last long. Soon the late-night comedian was back in the ring, taking swings at his favorite opponent.

Kelley theorizes that the fight has actually served as a handy publicity tool for both stars, and predicts it won't be over for good any time soon.

"Letterman vs. Winfrey will never reach pay-per-view because these heavy weights know the limits. She is accustomed to genuflection and he can't bend a knee -- for long," writes Kelley. "But both know their so-called feud serves them well, especially when they appear together on Super Bowl commercials. So let's stay tuned for the next round."